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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H26O2
Molecular Weight 298.4192
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NORETHINDRONE

SMILES

[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]3([H])[C@@]4([H])CCC(=O)C=C4CC[C@@]23[H]

InChI

InChIKey=VIKNJXKGJWUCNN-XGXHKTLJSA-N
InChI=1S/C20H26O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,12,15-18,22H,4-11H2,2H3/t15-,16+,17+,18-,19-,20-/m0/s1

HIDE SMILES / InChI

Molecular Formula C20H26O2
Molecular Weight 298.4192
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Norethisterone (INN, BAN), also known as Norethindrone (USAN) (brand names Micronor, AYGESTIN, numerous others) is a synthetic progestational hormone (progestin) with actions similar to those of progesterone but functioning as a more potent inhibitor of ovulation. It has weak estrogenic and androgenic properties. The hormone has been used for the treatment of secondary amenorrhea, endometriosis, and abnormal uterine bleeding due to hormonal imbalance in the absence of organic pathology, such as submucous fibroids or uterine cancer. AYGESTIN® is not intended, recommended or approved to be used with oncomitant estrogen therapy in postmenopausal women for endometrial protection. Progestins diffuse freely into target cells and bind to the progesterone receptor. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Once bound to the receptor, progestins slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH surge. Allergic reaction could be: Itching or hives, swelling in your face or hands, swelling or tingling in your mouth or throat, chest tightness, trouble breathing.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
6.8 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
MICRONOR
Primary
AYGESTIN
Primary
AYGESTIN
Primary
AYGESTIN

Cmax

ValueDoseCo-administeredAnalytePopulation
26.19 ng/mL
5 mg single, oral
NORETHINDRONE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
166.9 ng × h/mL
5 mg single, oral
NORETHINDRONE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
8.51 h
5 mg single, oral
NORETHINDRONE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
3%
5 mg single, oral
NORETHINDRONE plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
Secondary amenorrhea, abnormal uterine bleeding due to hormonal imbalance in the absence of organic pathology: 2.5 to 10 mg may be given daily for 5 to 10 days to produce secretory transformation of an endometrium that has been adequately primed with either endogenous or exogenous estrogen. Endometriosis: Initial daily dosage of 5 mg for two weeks. Dosage should be increased by 2.5 mg per day every two weeks until 15 mg per day.
Route of Administration: Oral
In Vitro Use Guide
10 - 10000 nM norethindrone stimulates growth of MCF-7 cells
Substance Class Chemical
Record UNII
T18F433X4S
Record Status Validated (UNII)
Record Version